4-Nitrobenzoic Acid → HCID 22132653, compound

HRID 1857140Notes

Reaction equation

HRID 1857140 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[N+:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24].Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:30]([C:29]2[CH:28]=[CH:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:34][CH:33]=2)=[O:31])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132653HCID 22132653, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (110 mg) and commercially available 4-nitrobenzoic acid (100 mg) were dissolved in N,N-dimethylformamide (4 ml), 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (176 mg) was added, and the admixture was stirred at room temperature for 22 hours. The reaction mixture was then purified in the same manner as described in Example 50 to obtain 126 mg of the title compound (yield: 77%).

Workup

  1. customThe reaction mixture was then purified in the same manner

Sources & evidence

ORD record
ord-3c0f8a2e51654b59a31beb761f0dacce
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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